When Your Boss Has a Vagina

I’m a lady. And I’m a boss. I’m a lady boss. I work in the entertainment business. I’m a TV writer and producer. I manage actors, writers and a crew of professionals who do everything from makeup to action stunts and set construction to catering. Although I’m not new to being a lady, I am new to “bossing.” And it has made me think a lot about the following question: Does it matter if your boss has a penis or a vagina? I know having a vagina makes people confuse me with the secretary, but how much else does it affect?

In my career I’ve certainly had a lot of examples of male bosses—ones I greatly respected, who championed me and helped me get to where I am today. And the other ones. My first boss in Hollywood asked me in front of a roomful of men if I liked it when my boyfriend fucked me. I answered, “Well, he doesn’t really fuck me all that much.” That was my first realization that I was working in a truly male-dominated industry and that my boyfriend was gay. (The latter was confirmed when he stayed up all night crying after JFK Jr. died.)

I’ve had dysfunctional bosses and functional alcoholic ones. I’ve had a boss accuse me of being ungrateful for getting time off when my mom was going through chemotherapy (she’s okay now). I told him, “Thank you. It was a blast!” I’ve had bosses who wanted me to be their partner and bosses who wanted me to be their “partner.” One boss would get wasted at night and start IMing me. Boss: “Girl, what are you up to?” Me: “Just about to go to bed.” Boss: “Dreaming of me?” My drunk, 20-years-my-senior boss—yeah, that’s what I’m going to dream about. Good or bad, almost all my bosses have been men. All except the first one.

My very first boss was a woman. And she taught me a lot. When I was 16 I got a summer job as an assistant at a real estate firm, answering phones. The place was owned by a husband-and-wife team, Ed and Gloria. They were kind, with big laughs and big hearts—exactly the kind of first bosses you’d be looking for. Gloria had a factory job most of her life, and being the boss was a lifelong dream. For her it was about making her own hours and getting to work with the love of her life—her parrot.

She built a large cage in the conference room made, ironically, out of chicken wire. And that parrot worked right alongside us. Gray parrots are pretty smart as far as birds go. They can be taught to speak. This bird had been taught to speak—one sentence: “Hey, baby, let me see your tattoo.” And that bird used those seven words to express every single emotion he had. He’s hot. He’s cold. He’s bored. And we’d hear, “Hey, baby. Hey, baby, let me see your tattoo, tattoo, tattoo, tattoo, tattoo!” Sadly, I had no tattoo to show him.

Having the parrot made Gloria a tad eccentric, but she was a fantastic person. I really looked up to her. She was full of helpful advice any teenager would pretend not to care about in the moment but would later take. The most practical advice came one afternoon when the men in the office were all out getting lunch. Gloria said she had “something very, very important to talk to me about.” It meant a lot to me to have a mentor, a woman who owned her own business, whom I respected. So I was ready. I’d take notes. I’d pay close attention. I’d ask questions.

Gloria began, “Everything you want in life you can get one way.” Me: “Hard work?” Gloria: “By giving a great blow job.” This was not the mentor-mentee advice I was expecting. Gloria used her hand to simulate what was, in retrospect, a quite large penis. “You have to take it deep. That’s the secret.” She proceeded to show me her blow-job techniques while the parrot squawked in the background, “Hey, baby! Let me see your tattoo, tattoo, tattoo!” And that was my first lady-boss experience.

As an employee, I had good and bad bosses of both sexes. They could teach you how to give a blow job or they could ask for one. So I should say gender isn’t a factor at all in bossing. But now, as a boss, I think it is a factor. It absolutely matters whether your boss has a penis or a vagina, because gender affects everything. Now, as a lady boss, I can be bad in all the ways any boss can. I’ll have a fight with my fiancé on the way to work and take it out on you. I’ll make you work on the weekend and tell you Friday night. I’ll stock the break room with snacks only I like. I’ll notice when your car isn’t there right at nine. I’ll doubt you’re really sick. I’ll resent your car trouble, out-of-town weddings and dentist appointments. And yet I’ll leave early just to beat traffic—while you’re still at work.

But the real difference between having a male boss and a female boss is social customs. No matter what our roles are, we’re tied to ones that have existed since way before anyone noticed the glass ceiling. You hold the door for me because I’m a woman, not because I’m your boss. You look at my ass because you’re a man, not my subordinate. And I wear V-necks because I’m a woman and I have nice tits.

All in all, having a lady boss instead of a dude boss is like having a relationship with any other woman. Which is always a little complicated. A little complex. A little confusing. A little crazy. You may see me crying in my car. You may know how many Weight Watchers points I get each day. I may be late for a meeting because Prada is on Gilt Groupe. But I actually care about seeing pictures of your kids, and I’ll throw the office a puppy party as a reward for a job well done. But at the end of the day, like every boss, I’ll support you if you’re good and fire you if you’re bad. The only difference is, after I fire you, you’ll still have to walk me to my car.